Details
Stereochemistry | ACHIRAL |
Molecular Formula | C16H12O6 |
Molecular Weight | 300.2635 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COc1ccc(cc1O)-c2cc(=O)c3c(cc(cc3o2)O)O
InChI
InChIKey=MBNGWHIJMBWFHU-UHFFFAOYSA-N
InChI=1S/C16H12O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-7,17-19H,1H3
Molecular Formula | C16H12O6 |
Molecular Weight | 300.2635 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Diosmetin is the aglycone of the flavonoid glycoside diosmin, which occurs naturally in citrus fruits. Diosmetin is found in the legume Acacia farnesiana Wild and Olea europaea L. leaves. Diosmin is hydrolyzed to its aglycone diosmetin by intestinal microflora enzymes before its absorption into the body. Pharmacologically, diosmetin is reported to exhibit anticancer, antimicrobial, antioxidant, oestrogenic and anti-inflammatory activities. Diosmetin increased inhibitory GSK-3beta phosphorylation, while selectively reducing gamma-secretase activity, Abetta generation, tau hyperphosphorylation and pro-inflammatory activation of microglia in vitro, without altering Notch processing. Therefore, diosmetin could be considered as potential candidate for novel anti- Alzheimer's disease therapy. Diosmetin is ER-beta agonist and potential novel drug for the acute myeloid leukemia treatment.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20696580 |
140.0 nM [IC50] | ||
Target ID: CHEMBL3356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20696580 |
2.4 µM [IC50] | ||
Target ID: CHEMBL4878 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20696580 |
29.0 nM [IC50] | ||
Target ID: CHEMBL242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28835383 |
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Target ID: map04064 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28101238 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Preventing | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Resistance of MCF-7 cells to dimethylbenz(a)anthracene-induced apoptosis is due to reduced CYP1A1 expression. | 2002 Aug |
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Structural requirements of flavonoids for inhibition of antigen-Induced degranulation, TNF-alpha and IL-4 production from RBL-2H3 cells. | 2002 Oct |
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DNA damage and cell cycle arrest induced by 2-(4-amino-3-methylphenyl)-5-fluorobenzothiazole (5F 203, NSC 703786) is attenuated in aryl hydrocarbon receptor deficient MCF-7 cells. | 2003 Feb 24 |
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Free radical scavenging abilities of flavonoids as mechanism of protection against mutagenicity induced by tert-butyl hydroperoxide or cumene hydroperoxide in Salmonella typhimurium TA102. | 2003 Sep 9 |
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Antitubercular constituents of Valeriana laxiflora. | 2004 Jun |
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Inhibitory effects of flavonoids on phosphodiesterase isozymes from guinea pig and their structure-activity relationships. | 2004 Nov 15 |
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Analysis and quantification of flavonoidic compounds from Portuguese olive (Olea europaea L.) leaf cultivars. | 2005 Feb |
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Complete assignments of NMR data of 13 hydroxymethoxyflavones. | 2007 Dec |
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Flavonoids modulate monocarboxylate transporter-1-mediated transport of gamma-hydroxybutyrate in vitro and in vivo. | 2007 Feb |
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Plant-derived polyphenols attenuate lipopolysaccharide-induced nitric oxide and tumour necrosis factor production in murine microglia and macrophages. | 2008 Apr |
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Prediction of intestinal absorption and metabolism of pharmacologically active flavones and flavanones. | 2008 Apr 1 |
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Effect of flavonoids on rat splenocytes, a structure-activity relationship study. | 2008 Aug 15 |
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Diosmetin induces human osteoblastic differentiation through the protein kinase C/p38 and extracellular signal-regulated kinase 1/2 pathway. | 2008 Jun |
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Flavonoids diosmetin and luteolin inhibit midazolam metabolism by human liver microsomes and recombinant CYP 3A4 and CYP3A5 enzymes. | 2008 Mar 15 |
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A new ferulic acid ester and other constituents from Dracocephalum peregrinum. | 2008 Oct |
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Ecdysteroids and a sucrose phenylpropanoid ester from Froelichia floridana. | 2009 Feb |
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Aurintricarboxylic acid inhibits influenza virus neuraminidase. | 2009 Feb |
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Bioactivation of the phytoestrogen diosmetin by CYP1 cytochromes P450. | 2009 Feb 8 |
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Iron behaving badly: inappropriate iron chelation as a major contributor to the aetiology of vascular and other progressive inflammatory and degenerative diseases. | 2009 Jan 8 |
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Antioxidant Activity of Caffeic Acid through a Novel Mechanism under UVA Irradiation. | 2009 Jul |
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Anticancer effects of the flavonoid diosmetin on cell cycle progression and proliferation of MDA-MB 468 breast cancer cells due to CYP1 activation. | 2009 Jun |
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Trihydroxynaphthalene reductase of Curvularia lunata--a target for flavonoid action? | 2009 Mar 16 |
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Flavonoids and cinnamic acid derivatives as inhibitors of 17beta-hydroxysteroid dehydrogenase type 1. | 2009 Mar 25 |
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[Chemical constituents of Galium verum]. | 2009 Nov |
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[Studies on flavones from Flos Chrysanthemi Indici]. | 2009 Oct |
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Cytotoxic activity of flavonoids from the flowers of Chrysanthemum morifolium on human colon cancer Colon205 cells. | 2009 Sep |
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Flavonoids diosmetin and hesperetin are potent inhibitors of cytochrome P450 2C9-mediated drug metabolism in vitro. | 2010 |
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Why do we need multifunctional neuroprotective and neurorestorative drugs for Parkinson's and Alzheimer's diseases as disease modifying agents. | 2010 Jun |
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Managing phenol contents in crop plants by phytochemical farming and breeding-visions and constraints. | 2010 Mar 2 |
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In vitro effects of some flavones on human pyruvate kinase isoenzyme M2. | 2015 Mar |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28835383
Mice: 50mg /kg/every other day for 6 weeks
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19424633
Diosmetin caused G1 arrest at 10 microM in MDA-MB 468 cells after 48-h treatment whereas this effect was not observed in MCF-10A cells.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 08:24:59 UTC 2021
by
admin
on
Sat Jun 26 08:24:59 UTC 2021
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Record UNII |
TWZ37241OT
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Record Status |
Validated (UNII)
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Record Version |
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DSLD |
4156 (Number of products:7)
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SUB35834
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8101
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DIOSMETIN
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520-34-3
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5281612
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1314347
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520-34-3
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TWZ37241OT
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4601
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208-291-8
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M4594
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C039602
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DB11259
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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PARENT -> IMPURITY |
NMT 3%
USP
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ACTIVE MOIETY |